Natural isothiocyanates of the genus Capparis as potential agonists of apoptosis and antitumor drugs

doi:10.5497/wjp.v12.i4.35

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Basic Study

World J Pharmacol. Dec 22, 2023; 12(4): 35-52
Published online Dec 22, 2023. doi: 10.5497/wjp.v12.i4.35

Table 1 Composition of components that were identified from yellow fruits of Capparis cartilaginea

Peak	RT	Area	%	Compound	RI
1	2.477	67563.26	0.16	Isopropylnitrile	623
2	4.145	48903.53	0.11	N-methylene-ethenamine	727
3	8.089	20864469.13	48.74	Isopropyl isothiocyanate	837
4	10.846	55386.82	0.13	2-butenyl isothiocyanate	887
5	11.832	21159669.73	49.43	2-butyl isothiocyanate	920
6	12.578	597488.12	1.40	Isobutyl isothiocyanate	926
7	25.268	17767.47	0.04	Benzyl isothiocyanate	1359

RT: Retention time; RI: Retention index.

Table 2 Composition of components that were identified from green fruits of Capparis cartilaginea

Peak	RT	Area	%	Compound	RI
1	1.756	283022.83	0.19	Dimethylsulfide	520
2	2.453	308033.24	0.21	Isobutyronitrile	626
3	3.864	23282.6	0.02	Sec-butyl cyanate	689
4	4.145	284696.04	0.19	N-methylene-ethenamine	727
5	6.991	10973.58	0.01	Ethyl isothiocyanate	796
6	8.193	68423753.03	46.68	Isopropyl isothiocyanate	837
7	10.59	6355.8	0.00	Propyl isothiocyanate	881
8	10.854	393825.2	0.27	2-butenyl isothiocyanate	887
9	11.929	72938834.61	49.76	2-butyl isothiocyanate	920
10	12.586	3848951.24	2.63	Isobutyl isothiocyanate	926
11	25.276	70246.54	0.05	Benzyl isothiocyanate	1359

RT: Retention time; RI: Retention index.

Table 3 Composition of components that were identified from seeds of Capparis cartilaginea

Peak	RT	Area	%	Compound	RI
1	1.779	557486.8	55.82	Dimethylsulfide	520
2	2.493	18043.82	1.81	Isobutyronitrile	626
3	2.822	41394.08	4.14	3-methylbutanal	652
4	2.958	31612.69	3.17	2-methyl-butanal	662
5	8.112	280745.6	28.11	Isopropyl isothiocyanate	837
6	11.84	67963.7	6.80	2-butyl isothiocyanate	920
7	12.618	1561.57	0.16	Isobutyl isothiocyanate	926

RT: Retention time; RI: Retention index.

Table 4 Composition of components that were identified from jam of Capparis cartilaginea

Peak	RT	Area	%	Compound	RI
1	1.788	272484.92	3.85	Dimethyl sulfide	520
2	2.453	59609.49	0.84	Isobutyronitrile	626
3	2.814	96185.08	1.36	3-methyl-butanal	652
4	2.926	34760.26	0.49	2-methyl-butanal	662
5	4.161	145138.02	2.05	N-methylene-ethenamine	727
6	8.113	85740.89	1.21	Isopropyl isothiocyanate	837
7	11.824	232997.63	3.29	2-butyl isothiocyanate	920
8	12.61	6608.49	0.09	Isobutyl isothiocyanate	926
9	13.347	77903.33	1.10	β-pinene	979
10	13.981	7385.93	0.10	β-myrcene	991
11	14.806	8950.21	0.13	α-terpinene	1018
12	15.079	5640.69	0.08	P-cymene	1025
13	15.215	601965.53	8.51	Limonene	1030
14	15.296	13202.57	0.19	Eucalyptol	1032
15	16.249	112624.11	1.59	γ-terpinene	1060
16	17.219	7218.34	0.10	Terpinolene	1088
17	20.402	11884.14	0.17	α-terpineol	1189
18	25.261	57235.71	0.81	2-(2-butoxyethoxy)-ethanol acetate	1366
19	26.638	142269.27	2.01	Pentanoic acid, 2-ethylhexyl ester	1404
20	28.014	76710.10	1.08	1-dodecanol	1473
21	28.59	25321.22	0.36	Pentadecane	1500
22	30.152	13471.82	0.19	Diphenyl sulfide	1552
23	30.264	83985.94	1.19	Hexadecane	1600
24	30.45	11616.10	0.16	Octadecanal	1357
25	30.636	152595.56	2.16	Dodecanoic acid 1-methylethyl ester	1618
26	31.408	80674.69	1.14	2-propenoic acid dodecyl ester	1675
27	31.473	41016.71	0.58	Heptadecane	1700
28	31.547	53606.2	0.76	(1-methyldecyl)-benzene	1708
29	31.64	73991.74	1.05	(1-methyldecyl)-benzene	1735
30	32.189	9636.895	0.14	2-methyl-octadecane	1863
31	32.449	27402.23	0.39	Nonadecane	1900
32	33.491	19861.16	0.28	Hexadecanoic acid methyl ester	1926
33	33.732	28833.81	0.41	Hexadecanoic acid	1968
34	34.021	9930.393	0.14	Heneicosane	2100
35	37.182	4384622	61.99	Hexanedioic acid bis(2-ethylhexyl) ester	2398

RT: Retention time; RI: Retention index.

Table 5 Production of main isothiocyanates in essential oils of the genus Capparis collected in different world regions

Species, tissues	Collected place	1	2	4	5	6	7	8	12	13	17	Ref.
C. flexuosa, leaves	Brazil				11.2						79.3	[26]
C. spinosa, leaves and flower buds	Croatia	92.1			0.4		0.3					[11,27]
C. spinosa, leaves	Jordan	25.6		28.9								[28]
C. cartilaginea, leaves	Jordan	31.8	2.5	18.2		5.4						[28]
C. spinosa var. aegyptiaca	Egypt	24.7		12.4	3.2							[29]
C. cartilaginea, leaves	Egypt				65.0				29.9			[30]
C. deserti, leaves	Egypt				68.7				20.0			[30]
C. spinosa, fruits	Iran			13.7	10.6					15.6		[31]
C. cartilaginea, yellow fruits	Israel			48.7		1.4	49.4	0.1				This study
C. cartilaginea, green fruits	Israel		0.1	46.7		2.6	49.8	0.3				This study
C. cartilaginea, seeds	Israel			28.1		0.2	6.8					This study
C. cartilaginea, jam	Israel			1.2		0.1	3.3					This study
C. spinosa, leaves	Syria	25.6		28.9		16.6		2.2				[32]
C. ovata, buds	Turkey	4.5	1.5		0.1	0.2						[33]
C. ovata, leaves	Turkey	20.0	1.6		0.5	0.3						[33]
C. cartilaginea, leaves	Yemen			69.4	26.9	3.3						[34]

Table 6 Production of main isothiocyanates in essential oils of the genus Capparis collected in different world regions

Species, tissues	Collected place	1	4	5	6	Ref.
C. decidua, leaf	Pakistan		11.0	6.3		[34]
C. spinosa, leaves	Spain	87.2		0.1	0.8	[35]
C. spinosa, stems	Spain	86.6		0.1	0.4	[35]
C. spinosa, flower buds	Spain	65.3				[35]
C. spinosa, aerial parts	Saudi Arabia	31.6		1.1		[36]
C. cartilaginea, leaves	Kenya	31.8			3.2	[37]

Table 7 Predicted biological activity of isothiocyanates derived from essential oils of the genus Capparis

No	Anticancer properties. Pa¹	Anti-infectives properties. Pa¹
1	Apoptosis agonist (0.963)	Anti-schistosomal (0.759)
	Chemoprotective (0.871)	Antiviral (arbovirus) (0.638)
	Antineoplastic (0.794)	Anti-seborrheic (0.614)
2	Apoptosis agonist (0.965)	Anti-Helicobacter pylori (0.853)
	Chemoprotective (0.890)	Anti-seborrheic (0.749)
	Chemosensitizer (0.798)	Anti-schistosomal (0.711)
	Antineoplastic (0.789)	Antiparasitic (0.537)
3	Apoptosis agonist (0.956)	Anti-Helicobacter pylori (0.816)
	Chemoprotective (0.866)	Anti-seborrheic (0.690)
	Chemosensitizer (0.779)	Antiviral (arbovirus) (0.635)
	Antineoplastic (0.743)	Anti-schistosomal (0.612)
4	Apoptosis agonist (0.914)	Anti-Helicobacter pylori (0.720)
	Chemoprotective (0.819)	Anti-schistosomal (0.687)
	Chemosensitizer (0.726)	Anti-seborrheic (0.684)
5	Apoptosis agonist (0.956)	Anti-Helicobacter pylori (0.816)
	Chemoprotective (0.858)	Antiviral (arbovirus) (0.690)
	Chemosensitizer (0.778)	Anti-schistosomal (0.594)
	Antineoplastic (0.751)	Antiparasitic (0.570)
6	Apoptosis agonist (0.951)	Anti-Helicobacter pylori (0.804)
	Chemoprotective (0.850)	Anti-seborrheic (0.731)
	Chemosensitizer (0.765)	Anti-schistosomal (0.665)
	Antineoplastic (0.720)	Antiparasitic (0.524)
7	Apoptosis agonist (0.867)	Antiviral (arbovirus) (0.654)
	Chemoprotective (0.782)	Anti-seborrheic (0.650)
	Chemosensitizer (0.694)	Anti-Helicobacter pylori (0.624)
8	Apoptosis agonist (0.955)	Anti-Helicobacter pylori (0.822)
	Chemoprotective (0.839)	Antiparasitic (0.680)
	Antineoplastic (0.833)	Anti-helmintic (0.632)
	Chemosensitizer (0.791)	Antifungal (0.568)
9	Apoptosis agonist (0.965)	Anti-Helicobacter pylori (0.629)
	Antineoplastic (0.825)	Anti-schistosomal (0.598)
	Chemoprotective (0.782)
	Chemosensitizer (0.696)
10	Apoptosis agonist (0.933)	Anti-Helicobacter pylori (0.739)
	Chemoprotective (0.847)
	Antineoplastic (0.728)
	Chemosensitizer (0.722)
11	Apoptosis agonist (0.884)	Anti-Helicobacter pylori (0.679)
	Chemoprotective (0.812)
	Antineoplastic (0.714)
	Chemosensitizer (0.661)
12	Apoptosis agonist (0.956)	Anti-Helicobacter pylori (0.703)
	Chemoprotective (0.825)
	Chemosensitizer (0.741)
	Antineoplastic (0.740)
	Antineoplastic (genitourinary cancer) (0.581)
13	Apoptosis agonist (0.856)	Anti-Helicobacter pylori (0.703)
	Chemoprotective (0.825)
	Chemosensitizer (0.741)
	Antineoplastic (0.740)
	Antineoplastic (genitourinary cancer) (0.581)
14	Apoptosis agonist (0.959)	Anti-Helicobacter pylori (0.792)
	Chemoprotective (0.867)	Antiparasitic (0.609)
	Chemosensitizer (0.787)	Anti-helmintic (0.581)
	Antineoplastic (0.775)	Antis-chistosomal (0.574)
15	Apoptosis agonist (0.923)	Anti-Helicobacter pylori (0.659)
	Chemoprotective (0.817)	Antifungal (0.658)
	Antineoplastic (0.771)	Antiparasitic (0.560)
	Chemosensitizer (0.728)
16	Apoptosis agonist (0.919)	Anti-Helicobacter pylori (0.752)
	Chemoprotective (0.821)	Antiviral (arbovirus) (0.730)
	Antineoplastic (0.751)	Antifungal (0.678)
	Chemosensitizer (0.747)	Antiparasitic (0.672)
17	Apoptosis agonist (0.953)	Anti-Helicobacter pylori (0.753)
	Chemoprotective (0.830)	Antifungal (0.533)
	Antineoplastic (0.781)
	Chemosensitizer (0.754)
18	Antineoplastic (myeloid leukemia) (0.805)	Anti-eczematic (0.606)
18	Chemosensitizer (0.742)
19	Apoptosis agonist (0.952)	Anti-Helicobacter pylori (0.769)
	Chemoprotective (0.847)	Anti-eczematic (0.610)
	Chemosensitizer (0.764)	Antifungal (0.575)
	Antineoplastic (0.753)	Anti-schistosomal (0.502)
20	Apoptosis agonist (0.955)	Anti-Helicobacter pylori (0.901)
	Chemoprotective (0.911)	Anti-ulcerative (0.611)
	Antineoplastic (0.781)
	Chemosensitizer (0.694)
	Anticarcinogenic (0.573)
	Chemopreventive (0.559)
21	Apoptosis agonist (0.851)	Anti-Helicobacter pylori (0.691)
	Chemoprotective (0.839)
	Chemosensitizer (0.747)
	Antineoplastic (0.733)
	Antineoplastic (genitourinary cancer) (0.627)
22	Apoptosis agonist (0.951)	Anti-seborrheic (0.775)
	Antineoplastic (0.820)	Antifungal (0.543)
	Chemoprotective (0.752)	Anti-Helicobacter pylori (0.542)
	Chemosensitizer (0.673)
	Preneoplastic conditions treatment (0.559)
23	Apoptosis agonist (0.929)	Anti-Helicobacter pylori (0.780)
	Chemoprotective (0.832)	Antiviral (arbovirus) (0.626)
	Chemosensitizer (0.771)	Antiparasitic (0.589)
	Antineoplastic (0.762)	Anti-helmintic (0.559)
	Preneoplastic conditions treatment (0.515)
24	Apoptosis agonist (0.932)	Anti-Helicobacter pylori (0.736)
	Chemoprotective (0.819)	Anti-schistosomal (0.579)
	Chemosensitizer (0.742)	Antifungal (0.550)
	Antineoplastic (0.675)	Antiviral (arbovirus) (0.531)
	Preneoplastic conditions treatment (0.541)	Antiparasitic (0.529)
25	Apoptosis agonist (0.930)	Anti-Helicobacter pylori (0.715)
	Chemoprotective (0.828)	Antiviral (arbovirus) (0.639)
	Antineoplastic (0.792)	Antifungal (0.620)
	Chemosensitizer (0.754)
26	Apoptosis agonist (0.938)	Periodontitis treatment (0.752)
	Chemoprotective (0.827)	Anti-Helicobacter pylori (0.739)
	Antineoplastic (0.740)	Antifungal (0.622)
	Chemosensitizer (0.736)	Antiviral (arbovirus) (0.599)
	Preneoplastic conditions treatment (0.593)
27	Apoptosis agonist (0.937)	Periodontitis treatment (0.727)
	Chemoprotective (0.820)	Anti-Helicobacter pylori (0.718)
	Antineoplastic (0.742)	Antifungal (0.644)
	Chemosensitizer (0.728)	Antiviral (arbovirus) (0.563)
	Preneoplastic conditions treatment (0.563)
28	Apoptosis agonist (0.934)	Periodontitis treatment (0.751)
	Chemoprotective (0.823)	Anti-Helicobacter pylori (0.733)
	Antineoplastic (0.740)	Antifungal (0.639)
	Chemosensitizer (0.732)	Antiviral (arbovirus) (0.621)
	Preneoplastic conditions treatment (0.613)

¹Only activities with Pa > 0.5 are shown.

Citation: Hanuš L, Naor T, Gloriozova T, Dembitsky VM. Natural isothiocyanates of the genus Capparis as potential agonists of apoptosis and antitumor drugs. World J Pharmacol 2023; 12(4): 35-52
URL: https://www.wjgnet.com/2220-3192/full/v12/i4/35.htm
DOI: https://dx.doi.org/10.5497/wjp.v12.i4.35